OA12015A - Fused pyrrolecarboxamides: gaba brain receptor ligands. - Google Patents

Fused pyrrolecarboxamides: gaba brain receptor ligands. Download PDF

Info

Publication number: OA12015A
Authority: OA; OAPI
Prior art keywords: oxo; alkyl; carboxamide; phenyl; amino
Prior art date: 1999-08-31

Application number

OA1200200063A

Other languages

English (en)

Inventor

Pamela Albaugh

Alan Hutchison

Kenneth Shaw

Original Assignee

Neurogen Corp

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1999-08-31

Filing date

2000-08-30

Publication date

2006-04-19

2000-08-30 Application filed by Neurogen Corp filed Critical Neurogen Corp

2006-04-19 Publication of OA12015A publication Critical patent/OA12015A/en

Links

RLOQBKJCOAXOLR-UHFFFAOYSA-N 1h-pyrrole-2-carboxamide Chemical class NC(=O)C1=CC=CN1 RLOQBKJCOAXOLR-UHFFFAOYSA-N 0.000 title abstract description 6
210000004556 brain Anatomy 0.000 title abstract description 5
239000003446 ligand Substances 0.000 title description 8
150000001875 compounds Chemical class 0.000 claims abstract description 383
102000027484 GABAA receptors Human genes 0.000 claims abstract description 54
108091008681 GABAA receptors Proteins 0.000 claims abstract description 54
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 16
208000019901 Anxiety disease Diseases 0.000 claims abstract description 15
230000036506 anxiety Effects 0.000 claims abstract description 12
208000019116 sleep disease Diseases 0.000 claims abstract description 12
208000024827 Alzheimer disease Diseases 0.000 claims abstract description 6
125000000217 alkyl group Chemical group 0.000 claims description 267
229910052739 hydrogen Inorganic materials 0.000 claims description 198
239000001257 hydrogen Chemical group 0.000 claims description 198
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 174
-1 hydroxy, amino, benzyl Chemical group 0.000 claims description 145
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 128
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 119
125000003545 alkoxy group Chemical group 0.000 claims description 112
229910052736 halogen Inorganic materials 0.000 claims description 109
150000002367 halogens Chemical group 0.000 claims description 109
150000002431 hydrogen Chemical group 0.000 claims description 101
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 67
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 61
125000001424 substituent group Chemical group 0.000 claims description 60
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 50
125000004122 cyclic group Chemical group 0.000 claims description 37
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 37
229910052757 nitrogen Inorganic materials 0.000 claims description 34
125000000753 cycloalkyl group Chemical group 0.000 claims description 33
125000004093 cyano group Chemical group *C#N 0.000 claims description 31
125000004043 oxo group Chemical group O=* 0.000 claims description 29
238000000034 method Methods 0.000 claims description 28
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 27
125000004432 carbon atom Chemical group C* 0.000 claims description 27
239000000203 mixture Substances 0.000 claims description 26
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 25
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 24
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 19
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 19
230000027455 binding Effects 0.000 claims description 19
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 19
230000000694 effects Effects 0.000 claims description 19
229910052799 carbon Inorganic materials 0.000 claims description 18
125000004663 dialkyl amino group Chemical group 0.000 claims description 18
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 18
150000003839 salts Chemical class 0.000 claims description 18
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 17
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 17
239000001301 oxygen Substances 0.000 claims description 17
229910052760 oxygen Inorganic materials 0.000 claims description 17
125000004076 pyridyl group Chemical group 0.000 claims description 17
125000001072 heteroaryl group Chemical group 0.000 claims description 16
125000003118 aryl group Chemical group 0.000 claims description 15
238000003556 assay Methods 0.000 claims description 15
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
231100000252 nontoxic Toxicity 0.000 claims description 13
230000003000 nontoxic effect Effects 0.000 claims description 13
208000035475 disorder Diseases 0.000 claims description 11
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 10
125000002883 imidazolyl group Chemical group 0.000 claims description 10
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
SDFDKKZWRHKDIR-UHFFFAOYSA-N C1CCCCC2=C1NC=C2C(=O)N Chemical compound C1CCCCC2=C1NC=C2C(=O)N SDFDKKZWRHKDIR-UHFFFAOYSA-N 0.000 claims description 9
125000003282 alkyl amino group Chemical group 0.000 claims description 9
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 9
208000010877 cognitive disease Diseases 0.000 claims description 9
DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 9
XCKPUFSDEYHSKM-UHFFFAOYSA-N 2,3,3a,4-tetrahydro-1h-indole-3-carboxamide Chemical compound C1=CCC2C(C(=O)N)CNC2=C1 XCKPUFSDEYHSKM-UHFFFAOYSA-N 0.000 claims description 8
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 8
125000001041 indolyl group Chemical group 0.000 claims description 8
238000004519 manufacturing process Methods 0.000 claims description 8
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 8
125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims description 7
125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims description 7
125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 claims description 7
125000002947 alkylene group Chemical group 0.000 claims description 7
150000003857 carboxamides Chemical class 0.000 claims description 7
201000010099 disease Diseases 0.000 claims description 7
239000000546 pharmaceutical excipient Substances 0.000 claims description 7
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 7
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 6
208000028698 Cognitive impairment Diseases 0.000 claims description 6
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 6
125000000623 heterocyclic group Chemical group 0.000 claims description 6
125000002757 morpholinyl group Chemical group 0.000 claims description 6
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 6
XERBBQHVHYAUSF-UHFFFAOYSA-N 4-oxo-n-[4-(2-pyrrolidin-1-ylethoxy)pyridin-3-yl]-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound C=1NC=2CCCC(=O)C=2C=1C(=O)NC1=CN=CC=C1OCCN1CCCC1 XERBBQHVHYAUSF-UHFFFAOYSA-N 0.000 claims description 5
LSGKMZLPZFPAIN-UHFFFAOYSA-N Oxime-1H-Indole-3-carboxaldehyde Natural products C1=CC=C2C(C(=O)N)=CNC2=C1 LSGKMZLPZFPAIN-UHFFFAOYSA-N 0.000 claims description 5
239000002253 acid Substances 0.000 claims description 5
125000001786 isothiazolyl group Chemical group 0.000 claims description 5
125000003386 piperidinyl group Chemical group 0.000 claims description 5
125000003226 pyrazolyl group Chemical group 0.000 claims description 5
125000002098 pyridazinyl group Chemical group 0.000 claims description 5
125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
125000000168 pyrrolyl group Chemical group 0.000 claims description 5
NKRCVLNDEWURBV-UHFFFAOYSA-N 4,5,6,7-tetrahydro-1h-indole-3-carboxamide Chemical compound C1CCCC2=C1NC=C2C(=O)N NKRCVLNDEWURBV-UHFFFAOYSA-N 0.000 claims description 4
AUJGAMJLFQFBNM-UHFFFAOYSA-N 4-oxo-n-[4-(2-pyrrolidin-1-ylethoxy)phenyl]-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound C=1NC=2CCCC(=O)C=2C=1C(=O)NC(C=C1)=CC=C1OCCN1CCCC1 AUJGAMJLFQFBNM-UHFFFAOYSA-N 0.000 claims description 4
125000003342 alkenyl group Chemical group 0.000 claims description 4
125000000304 alkynyl group Chemical group 0.000 claims description 4
239000003937 drug carrier Substances 0.000 claims description 4
230000002401 inhibitory effect Effects 0.000 claims description 4
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 3
125000003635 2-dimethylaminoethoxy group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 claims description 3
REFILFCXOOMYGW-UHFFFAOYSA-N 4-oxo-n-[4-(2-piperidin-1-ylethoxy)pyridin-3-yl]-1,5,6,7-tetrahydroindole-3-carboxamide;hydrochloride Chemical compound Cl.C=1NC=2CCCC(=O)C=2C=1C(=O)NC1=CN=CC=C1OCCN1CCCCC1 REFILFCXOOMYGW-UHFFFAOYSA-N 0.000 claims description 3
ZHVPSFPOEYSEBP-UHFFFAOYSA-N 4-oxo-n-[4-(2-piperidin-2-ylethoxy)phenyl]-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound C=1NC=2CCCC(=O)C=2C=1C(=O)NC(C=C1)=CC=C1OCCC1CCCCN1 ZHVPSFPOEYSEBP-UHFFFAOYSA-N 0.000 claims description 3
CTCXQQDDYMIYMA-UHFFFAOYSA-N 4-oxo-n-[4-(piperidin-3-ylmethoxy)phenyl]-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound C=1NC=2CCCC(=O)C=2C=1C(=O)NC(C=C1)=CC=C1OCC1CCCNC1 CTCXQQDDYMIYMA-UHFFFAOYSA-N 0.000 claims description 3
QZLZUFJHMFLKRX-UHFFFAOYSA-N 4-oxo-n-[4-[2-(propan-2-ylamino)ethoxy]pyridin-3-yl]-1,5,6,7-tetrahydroindole-3-carboxamide;hydrochloride Chemical compound Cl.CC(C)NCCOC1=CC=NC=C1NC(=O)C1=CNC2=C1C(=O)CCC2 QZLZUFJHMFLKRX-UHFFFAOYSA-N 0.000 claims description 3
NFGGOYREQIVVND-UHFFFAOYSA-N C1CCC(=O)C2C(C(=O)O)=CNC21 Chemical compound C1CCC(=O)C2C(C(=O)O)=CNC21 NFGGOYREQIVVND-UHFFFAOYSA-N 0.000 claims description 3
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 3
229910003827 NRaRb Inorganic materials 0.000 claims description 3
125000003670 adamantan-2-yl group Chemical group [H]C1([H])C(C2([H])[H])([H])C([H])([H])C3([H])C([*])([H])C1([H])C([H])([H])C2([H])C3([H])[H] 0.000 claims description 3
150000001408 amides Chemical class 0.000 claims description 3
YZHJISPIBWKWGY-UHFFFAOYSA-N cp-615,003 Chemical compound C1=C(F)C(OCCNCCC)=CC=C1NC(=O)C1=CNC2=C1C(=O)CCC2 YZHJISPIBWKWGY-UHFFFAOYSA-N 0.000 claims description 3
125000005842 heteroatom Chemical group 0.000 claims description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
YJKWHQAVHFZGNL-UHFFFAOYSA-N n-[3-fluoro-4-(2-morpholin-4-yl-2-oxoethoxy)phenyl]-4-oxo-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound FC1=CC(NC(=O)C=2C=3C(=O)CCCC=3NC=2)=CC=C1OCC(=O)N1CCOCC1 YJKWHQAVHFZGNL-UHFFFAOYSA-N 0.000 claims description 3
XVSDTBIBMCVRIS-UHFFFAOYSA-N n-[4-(2-imidazol-1-ylethoxy)phenyl]-4-oxo-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound C=1NC=2CCCC(=O)C=2C=1C(=O)NC(C=C1)=CC=C1OCCN1C=CN=C1 XVSDTBIBMCVRIS-UHFFFAOYSA-N 0.000 claims description 3
OOFSSWHBZDEYHN-UHFFFAOYSA-N n-[4-[2-(benzylamino)ethoxy]pyridin-3-yl]-4-oxo-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound C=1NC=2CCCC(=O)C=2C=1C(=O)NC1=CN=CC=C1OCCNCC1=CC=CC=C1 OOFSSWHBZDEYHN-UHFFFAOYSA-N 0.000 claims description 3
FLKXMJLRIAXPHS-UHFFFAOYSA-N n-[4-[2-(butylamino)ethoxy]pyridin-3-yl]-4-oxo-1,5,6,7-tetrahydroindole-3-carboxamide;hydrochloride Chemical compound Cl.CCCCNCCOC1=CC=NC=C1NC(=O)C1=CNC2=C1C(=O)CCC2 FLKXMJLRIAXPHS-UHFFFAOYSA-N 0.000 claims description 3
RBLFTRYRZHEBJL-UHFFFAOYSA-N n-[4-[2-(cyclopropylmethylamino)ethoxy]phenyl]-4-oxo-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound C=1NC=2CCCC(=O)C=2C=1C(=O)NC(C=C1)=CC=C1OCCNCC1CC1 RBLFTRYRZHEBJL-UHFFFAOYSA-N 0.000 claims description 3
FLQKURIQMSXGCI-UHFFFAOYSA-N n-[4-[2-(dimethylamino)ethoxy]-3-fluorophenyl]-4-oxo-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound C1=C(F)C(OCCN(C)C)=CC=C1NC(=O)C1=CNC2=C1C(=O)CCC2 FLQKURIQMSXGCI-UHFFFAOYSA-N 0.000 claims description 3
SZVJIEZEEHMVRF-UHFFFAOYSA-N n-[4-[2-(dimethylamino)ethoxy]pyridin-3-yl]-4-oxo-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound CN(C)CCOC1=CC=NC=C1NC(=O)C1=CNC2=C1C(=O)CCC2 SZVJIEZEEHMVRF-UHFFFAOYSA-N 0.000 claims description 3
SYGJKLFDYVILIQ-UHFFFAOYSA-N n-[4-[2-(tert-butylamino)ethoxy]phenyl]-4-oxo-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound C1=CC(OCCNC(C)(C)C)=CC=C1NC(=O)C1=CNC2=C1C(=O)CCC2 SYGJKLFDYVILIQ-UHFFFAOYSA-N 0.000 claims description 3
OSJIVBPULCQGFM-UHFFFAOYSA-N n-[4-[2-[3-(diethylamino)propylamino]-2-oxoethoxy]phenyl]-4-oxo-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound C1=CC(OCC(=O)NCCCN(CC)CC)=CC=C1NC(=O)C1=CNC2=C1C(=O)CCC2 OSJIVBPULCQGFM-UHFFFAOYSA-N 0.000 claims description 3
UKSJBGOYMCORBE-UHFFFAOYSA-N n-[4-[3-(2-methylpropylamino)propoxy]phenyl]-4-oxo-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound C1=CC(OCCCNCC(C)C)=CC=C1NC(=O)C1=CNC2=C1C(=O)CCC2 UKSJBGOYMCORBE-UHFFFAOYSA-N 0.000 claims description 3
125000003884 phenylalkyl group Chemical group 0.000 claims description 3
208000020685 sleep-wake disease Diseases 0.000 claims description 3
239000000126 substance Substances 0.000 claims description 3
OSLYICIMONDSPX-UHFFFAOYSA-N 4-oxo-n-[4-(1,2,4-triazol-1-yl)phenyl]-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound C=1NC=2CCCC(=O)C=2C=1C(=O)NC(C=C1)=CC=C1N1C=NC=N1 OSLYICIMONDSPX-UHFFFAOYSA-N 0.000 claims description 2
PWDYVOVYEKFUQO-UHFFFAOYSA-N 4-oxo-n-[4-(2-piperidin-1-ylethoxy)pyridin-3-yl]-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound C=1NC=2CCCC(=O)C=2C=1C(=O)NC1=CN=CC=C1OCCN1CCCCC1 PWDYVOVYEKFUQO-UHFFFAOYSA-N 0.000 claims description 2
CUJNEIUKBQVEGW-UHFFFAOYSA-N 4-oxo-n-[4-(pyridin-3-ylmethoxy)pyridin-3-yl]-1,5,6,7-tetrahydroindole-3-carboxamide;hydrochloride Chemical compound Cl.C=1NC=2CCCC(=O)C=2C=1C(=O)NC1=CN=CC=C1OCC1=CC=CN=C1 CUJNEIUKBQVEGW-UHFFFAOYSA-N 0.000 claims description 2
XMXQKYANEGBUKG-UHFFFAOYSA-N 4-oxo-n-[4-(pyridin-4-ylmethoxy)pyridin-3-yl]-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound C=1NC=2CCCC(=O)C=2C=1C(=O)NC1=CN=CC=C1OCC1=CC=NC=C1 XMXQKYANEGBUKG-UHFFFAOYSA-N 0.000 claims description 2
FVSOYZVNSNXLGY-UHFFFAOYSA-N 4-oxo-n-[4-(pyridin-4-ylmethoxy)pyridin-3-yl]-1,5,6,7-tetrahydroindole-3-carboxamide;hydrochloride Chemical compound Cl.C=1NC=2CCCC(=O)C=2C=1C(=O)NC1=CN=CC=C1OCC1=CC=NC=C1 FVSOYZVNSNXLGY-UHFFFAOYSA-N 0.000 claims description 2
NVHWFYGQNCBPGV-UHFFFAOYSA-N 4-oxo-n-[4-[2-(2-pyrrolidin-1-ylethoxy)ethoxy]pyridin-3-yl]-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound C=1NC=2CCCC(=O)C=2C=1C(=O)NC1=CN=CC=C1OCCOCCN1CCCC1 NVHWFYGQNCBPGV-UHFFFAOYSA-N 0.000 claims description 2
NCEAEUVGVIMDTB-UHFFFAOYSA-N 4-oxo-n-[4-[2-(propan-2-ylamino)ethoxy]phenyl]-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound C1=CC(OCCNC(C)C)=CC=C1NC(=O)C1=CNC2=C1C(=O)CCC2 NCEAEUVGVIMDTB-UHFFFAOYSA-N 0.000 claims description 2
IQUBJCDKEDETJG-UHFFFAOYSA-N 4-oxo-n-[4-[2-(propan-2-ylamino)ethoxy]pyridin-3-yl]-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound CC(C)NCCOC1=CC=NC=C1NC(=O)C1=CNC2=C1C(=O)CCC2 IQUBJCDKEDETJG-UHFFFAOYSA-N 0.000 claims description 2
GYDRRAFCJYHPLG-UHFFFAOYSA-N 4-oxo-n-[4-[2-(propylamino)ethoxy]phenyl]-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound C1=CC(OCCNCCC)=CC=C1NC(=O)C1=CNC2=C1C(=O)CCC2 GYDRRAFCJYHPLG-UHFFFAOYSA-N 0.000 claims description 2
VNHFPPQQVMYYPU-UHFFFAOYSA-N 4-oxo-n-[4-[2-(thiophen-2-ylsulfonylamino)ethoxy]phenyl]-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound C=1NC=2CCCC(=O)C=2C=1C(=O)NC(C=C1)=CC=C1OCCNS(=O)(=O)C1=CC=CS1 VNHFPPQQVMYYPU-UHFFFAOYSA-N 0.000 claims description 2
MLWALNIOJBDNPP-UHFFFAOYSA-N 4-oxo-n-[4-[3-(pentylamino)propoxy]phenyl]-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound C1=CC(OCCCNCCCCC)=CC=C1NC(=O)C1=CNC2=C1C(=O)CCC2 MLWALNIOJBDNPP-UHFFFAOYSA-N 0.000 claims description 2
LYMHOHHCZNMXPJ-UHFFFAOYSA-N 4-oxo-n-[4-[3-(pentylamino)propoxy]phenyl]-5,6,7,8-tetrahydro-1h-cyclohepta[b]pyrrole-3-carboxamide Chemical compound C1=CC(OCCCNCCCCC)=CC=C1NC(=O)C1=CNC2=C1C(=O)CCCC2 LYMHOHHCZNMXPJ-UHFFFAOYSA-N 0.000 claims description 2
KPFUDXQROMACAQ-UHFFFAOYSA-N 4-oxo-n-[4-[3-(propan-2-ylamino)propoxy]phenyl]-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound C1=CC(OCCCNC(C)C)=CC=C1NC(=O)C1=CNC2=C1C(=O)CCC2 KPFUDXQROMACAQ-UHFFFAOYSA-N 0.000 claims description 2
BCFRNHUICWULJW-UHFFFAOYSA-N 4-oxo-n-[4-[3-(propylamino)propoxy]pyridin-3-yl]-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound CCCNCCCOC1=CC=NC=C1NC(=O)C1=CNC2=C1C(=O)CCC2 BCFRNHUICWULJW-UHFFFAOYSA-N 0.000 claims description 2
SBKNHTGIXVOTHI-UHFFFAOYSA-N 4-oxo-n-[4-[3-(pyridin-4-ylmethylamino)propoxy]pyridin-3-yl]-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound C=1NC=2CCCC(=O)C=2C=1C(=O)NC1=CN=CC=C1OCCCNCC1=CC=NC=C1 SBKNHTGIXVOTHI-UHFFFAOYSA-N 0.000 claims description 2
MUGKPTHZEQLNBX-CQSZACIVSA-N 4-oxo-n-[4-[[(2r)-pyrrolidin-2-yl]methoxy]phenyl]-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound C=1NC=2CCCC(=O)C=2C=1C(=O)NC(C=C1)=CC=C1OC[C@H]1CCCN1 MUGKPTHZEQLNBX-CQSZACIVSA-N 0.000 claims description 2
CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 claims description 2
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
UOOKATMZXWBBBK-UHFFFAOYSA-N n-[2-fluoro-4-[2-(propylamino)ethoxy]phenyl]-4-oxo-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound FC1=CC(OCCNCCC)=CC=C1NC(=O)C1=CNC2=C1C(=O)CCC2 UOOKATMZXWBBBK-UHFFFAOYSA-N 0.000 claims description 2
DUJLLRDLZUMEDZ-UHFFFAOYSA-N n-[3-[2-[(4-methylcyclohexyl)amino]ethoxy]phenyl]-4-oxo-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound C1CC(C)CCC1NCCOC1=CC=CC(NC(=O)C=2C=3C(=O)CCCC=3NC=2)=C1 DUJLLRDLZUMEDZ-UHFFFAOYSA-N 0.000 claims description 2
XOYNVANVAQNERJ-UHFFFAOYSA-N n-[3-[3-(1-adamantylamino)propoxy]phenyl]-4-oxo-5,6,7,8-tetrahydro-1h-cyclohepta[b]pyrrole-3-carboxamide Chemical compound C1CCCC(=O)C2=C1NC=C2C(=O)NC1=CC=CC(OCCCNC23CC4CC(CC(C4)C2)C3)=C1 XOYNVANVAQNERJ-UHFFFAOYSA-N 0.000 claims description 2
DLJLSDXHLFOWPJ-UHFFFAOYSA-N n-[3-[3-(2-methylbutylamino)propoxy]phenyl]-4-oxo-5,6,7,8-tetrahydro-1h-cyclohepta[b]pyrrole-3-carboxamide Chemical compound CCC(C)CNCCCOC1=CC=CC(NC(=O)C=2C=3C(=O)CCCCC=3NC=2)=C1 DLJLSDXHLFOWPJ-UHFFFAOYSA-N 0.000 claims description 2
RUVNAFFEXUTXQZ-UHFFFAOYSA-N n-[3-[3-(2-methylpropylamino)propoxy]phenyl]-4-oxo-5,6,7,8-tetrahydro-1h-cyclohepta[b]pyrrole-3-carboxamide Chemical compound CC(C)CNCCCOC1=CC=CC(NC(=O)C=2C=3C(=O)CCCCC=3NC=2)=C1 RUVNAFFEXUTXQZ-UHFFFAOYSA-N 0.000 claims description 2
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125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
IRSZDNMUBYZIOH-UHFFFAOYSA-N tert-butyl n-[2-[4-[(4-oxo-1,5,6,7-tetrahydroindole-3-carbonyl)amino]phenyl]ethyl]carbamate Chemical compound C1=CC(CCNC(=O)OC(C)(C)C)=CC=C1NC(=O)C1=CNC2=C1C(=O)CCC2 IRSZDNMUBYZIOH-UHFFFAOYSA-N 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
125000001113 thiadiazolyl group Chemical group 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
229930192474 thiophene Natural products 0.000 description 1
230000009529 traumatic brain injury Effects 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
- A61K51/04—Organic compounds
- A61K51/041—Heterocyclic compounds
- A61K51/044—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine, rifamycins
- A61K51/0468—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine, rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- A61K51/047—Benzodiazepines
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/52—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring condensed with a ring other than six-membered
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N2333/00—Assays involving biological materials from specific organisms or of a specific nature
- G01N2333/435—Assays involving biological materials from specific organisms or of a specific nature from animals; from humans
- G01N2333/705—Assays involving receptors, cell surface antigens or cell surface determinants
- G01N2333/70571—Assays involving receptors, cell surface antigens or cell surface determinants for neuromediators, e.g. serotonin receptor, dopamine receptor

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
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Animal Behavior & Ethology (AREA)
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Physics & Mathematics (AREA)
Optics & Photonics (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Psychiatry (AREA)
Anesthesiology (AREA)
Hospice & Palliative Care (AREA)
Pain & Pain Management (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Plural Heterocyclic Compounds (AREA)
Indole Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pyrrole Compounds (AREA)

OA1200200063A 1999-08-31 2000-08-30 Fused pyrrolecarboxamides: gaba brain receptor ligands. OA12015A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US15178999P	1999-08-31	1999-08-31
US38731199A	1999-08-31	1999-08-31

Publications (1)

Publication Number	Publication Date
OA12015A true OA12015A (en)	2006-04-19

Family

ID=26848974

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
OA1200200063A OA12015A (en)	1999-08-31	2000-08-30	Fused pyrrolecarboxamides: gaba brain receptor ligands.

Country Status (25)

Country	Link
US (1)	US7109351B1 (is)
EP (1)	EP1210328A1 (is)
JP (1)	JP2003508385A (is)
KR (1)	KR20020027613A (is)
CN (1)	CN1372546A (is)
AP (1)	AP2002002420A0 (is)
AU (1)	AU7092800A (is)
BG (1)	BG106459A (is)
BR (1)	BR0013664A (is)
CA (1)	CA2381553A1 (is)
CR (1)	CR6581A (is)
CZ (1)	CZ2002614A3 (is)
EA (1)	EA200200188A1 (is)
EE (1)	EE200200111A (is)
HR (1)	HRP20020104A2 (is)
HU (1)	HUP0202534A3 (is)
IL (1)	IL147971A0 (is)
IS (1)	IS6290A (is)
MX (1)	MXPA02001709A (is)
NO (1)	NO20020948L (is)
OA (1)	OA12015A (is)
PL (1)	PL354513A1 (is)
SK (1)	SK2582002A3 (is)
TR (1)	TR200200544T2 (is)
WO (1)	WO2001016103A1 (is)

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2000
- 2000-08-30 IL IL14797100A patent/IL147971A0/xx unknown
- 2000-08-30 MX MXPA02001709A patent/MXPA02001709A/es active IP Right Grant
- 2000-08-30 WO PCT/US2000/023862 patent/WO2001016103A1/en not_active Ceased
- 2000-08-30 CZ CZ2002614A patent/CZ2002614A3/cs unknown
- 2000-08-30 HU HU0202534A patent/HUP0202534A3/hu unknown
- 2000-08-30 HR HR20020104A patent/HRP20020104A2/hr not_active Application Discontinuation
- 2000-08-30 AP APAP/P/2002/002420A patent/AP2002002420A0/en unknown
- 2000-08-30 CA CA002381553A patent/CA2381553A1/en not_active Abandoned
- 2000-08-30 CN CN00812233A patent/CN1372546A/zh active Pending
- 2000-08-30 AU AU70928/00A patent/AU7092800A/en not_active Abandoned
- 2000-08-30 BR BR0013664-6A patent/BR0013664A/pt not_active Application Discontinuation
- 2000-08-30 EA EA200200188A patent/EA200200188A1/ru unknown
- 2000-08-30 EP EP00959643A patent/EP1210328A1/en not_active Withdrawn
- 2000-08-30 SK SK258-2002A patent/SK2582002A3/sk unknown
- 2000-08-30 EE EEP200200111A patent/EE200200111A/xx unknown
- 2000-08-30 TR TR2002/00544T patent/TR200200544T2/xx unknown
- 2000-08-30 OA OA1200200063A patent/OA12015A/en unknown
- 2000-08-30 US US09/651,207 patent/US7109351B1/en not_active Expired - Fee Related
- 2000-08-30 JP JP2001519673A patent/JP2003508385A/ja not_active Withdrawn
- 2000-08-30 KR KR1020027002757A patent/KR20020027613A/ko not_active Ceased
- 2000-08-30 PL PL00354513A patent/PL354513A1/xx not_active Application Discontinuation
2002
- 2002-02-07 CR CR6581A patent/CR6581A/es not_active Application Discontinuation
- 2002-02-27 IS IS6290A patent/IS6290A/is unknown
- 2002-02-27 NO NO20020948A patent/NO20020948L/no unknown
- 2002-02-28 BG BG106459A patent/BG106459A/bg unknown

Also Published As

Publication number	Publication date
AP2002002420A0 (en)	2002-03-31
PL354513A1 (en)	2004-01-26
AU7092800A (en)	2001-03-26
BR0013664A (pt)	2002-05-14
WO2001016103A1 (en)	2001-03-08
CZ2002614A3 (cs)	2002-08-14
HUP0202534A2 (hu)	2002-11-28
EA200200188A1 (ru)	2002-08-29
EE200200111A (et)	2003-06-16
KR20020027613A (ko)	2002-04-13
CR6581A (es)	2004-03-31
HUP0202534A3 (en)	2002-12-28
NO20020948D0 (no)	2002-02-27
JP2003508385A (ja)	2003-03-04
IS6290A (is)	2002-02-27
CA2381553A1 (en)	2001-03-08
CN1372546A (zh)	2002-10-02
SK2582002A3 (en)	2003-02-04
BG106459A (bg)	2002-12-29
HRP20020104A2 (en)	2004-02-29
NO20020948L (no)	2002-02-28
US7109351B1 (en)	2006-09-19
MXPA02001709A (es)	2002-10-23
TR200200544T2 (tr)	2002-06-21
EP1210328A1 (en)	2002-06-05
IL147971A0 (en)	2002-09-12

Publication	Publication Date	Title
EP1177177B1 (en)	2005-02-23	Substituted 4-oxo-quinoline-3-carboxamides: gaba brain receptor ligands
EP1228069B1 (en)	2003-04-02	Bicyclic and tricyclic heteroaromatic compounds
EP1019372B1 (en)	2006-04-05	Fused pyrrolecarboxamides; a new class of gaba brain receptor ligands
US5750702A (en)	1998-05-12	Certain pyrrolo pyridine-3-carboxamides; a new class of GABA brain receptor ligands
US6211365B1 (en)	2001-04-03	Fused pyrrolecarboxamides; a new class of GABA brain receptor ligands
US6656941B2 (en)	2003-12-02	Aryl substituted tetrahydroindazoles
US7109351B1 (en)	2006-09-19	Fused pyrrolecarboxamides; GABA brain receptor ligands
WO2000059905A1 (en)	2000-10-12	ARYL AND HETEROARYL FUSED AMINOALKYL-IMIDAZOLE DERIVATIVES: SELECTIVE MODULATORS OF GABAa RECEPTORS
US20050014939A1 (en)	2005-01-20	Fused pyrrolecarboxamides: GABA brain receptor ligands
US6743817B2 (en)	2004-06-01	Substituted fused pyrroleimines and pyrazoleimines
JP2005516901A (ja)	2005-06-09	１Ｈ−ピロロ［３，２−ｂ］ピリジン−３−カルボン酸アミド化合物
US6528649B2 (en)	2003-03-04	Imidazoloisoquinolines
US6673811B1 (en)	2004-01-06	1H-pyrrolo [3,2-b] pyridine-3-carboxylic acid amines as GABAA receptor ligands